Entrepreneurial diaspora communities are recognized as contributors to home country development. Yet, evidence of entrepreneurial African Caribbean (Afro-Caribbean) diaspora contribution to Caribbean development remains under-explored. This Chapter explores the motivation, goals and experiences of Afro-Caribbean entrepreneurs in the UK (importers, retailers and distributors) and the Caribbean (exporters) in Caribbean-UK trade to understand the role of the entrepreneurial diaspora in Caribbean development. The resulting socio-economic benefits and the industries, sectors and countries that benefited the most from Caribbean-UK business connections are highlighted. The chapter highlights Afro-Caribbean self-actualisation, self-direction and agency as valuable contributors to Caribbean socio-economic development. Building on the current stock of diaspora population that is emotionally connected to the people and culture of the Caribbean to further stimulate development with the diaspora, the paper recommends how a diaspora sales force could foster future Caribbean diaspora relations to support Caribbean growth through trade and entrepreneurship.